Toluene → HCID 72369211, compound

HRID 1669294Notes

Reaction equation

HRID 1669294 reaction equation
C[C:2](C)([O-:4])C.[K+].[Cl:7][C:8]1[N:13]=[CH:12][C:11]([C:14](=O)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:10][CH:9]=1.[C:22]1(C)C=CC=CC=1>>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([C:14](=[CH:22][O:4][CH3:2])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:12][N:13]=1

Participants

4

Reactant 3

HCID 1140Toluene2×HCID 11424652HCID 11424652, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 72369211HCID 72369211, compound

Procedure

(Methoxymethyl)triphenylphosphinium chloride (6.5 g, 20.0 mmol) is suspended in anhydrous toluene (50 mL) and potassium tert-butoxide (2.24 g, 20.0 mmol) carefully added. The solution is allowed to cool and stir at room temperature for 1 h. 1-(6-Chloro-pyridin-3-yl)-heptan-1-one (3.0 g, 13.3 mmol) is then dissolved into anhydrous toluene (50 mL) and added to the reaction mixture by syringe. The reaction is allowed to stir at room temperature for several hours and is monitored by HPLC. Upon complete consumption of starting material, the reaction is carefully quenched with saturated ammonium chloride solution, extracted with diethyl ether, washed, dried, and concentrated. The 2-chloro-5-(1-methoxymethylene-heptyl)-pyridine is purified using flash column chromatography.

Workup

  1. temperatureto cool
  2. additionadded to the reaction mixture by syringe
  3. stirringto stir at room temperature for several hours
  4. customUpon complete consumption of starting material
  5. customthe reaction is carefully quenched with saturated ammonium chloride solution
  6. extractionextracted with diethyl ether
  7. washwashed
  8. customdried
  9. concentrationconcentrated
  10. customThe 2-chloro-5-(1-methoxymethylene-heptyl)-pyridine is purified

Sources & evidence

ORD record
ord-e19468e45cf244dfa073fdef9631363f
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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